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Rolf Armstrong was born in Bay City, Michigan on April 21, 1889, to Richard and Harriet (Scott) Armstrong. His father owned the Boy-Line Fire Boat Company, which included a line of passenger ships. Some were deployed in Chicago for use at the Chicago World's Fair there in 1893. However, the father's business and family were struggling, and the family homestead was lost to foreclosure. In 1899, the family moved to Detroit, Michigan.

Rolf's father died in 1903, and a year later he and his mother moved to Seattle, Washington, following the footsteps of his oldest brother, William, who had moved there a year earlier. By now Rolf's artistic interests were emerging to more than a part-time pleasure.

Armstrong's work for the Pictorial Review was largely responsible for that magazine achieving a circulation of more than two million by 1926. A year later, he was the best-selling calendar artist at Brown & Bigelow. In 1930, RCA hired him to paint pin-ups to advertise their products, and in 1933 the Thomas D. Murphy Calendar Company signed him to produce a series of paintings for their line.

Rolf Armstrong died in 1960 on the island of Oahu, Hawaii as one of the best "pin-up" artists of the first half of the twentieth century.

In March 1940, Jewel Flowers, a girl from Lumberton, North Carolina, sent a picture of herself to Armstrong in response to an advert he had placed in the New York Times. Armstrong, 50 at the time, had been based at the Hotel des Artistes on West 67th Street in Manhattan since 1939, and was looking for new models. He invited Flowers for an interview. On March 25, 1940, Flowers started modeling for Armstrong. Their professional collaboration and friendship lasted for two decades. The first painting, titled "How am I doing?", reportedly because Flowers, unused to modeling, repeatedly asked Armstrong "How am I doing?" during the modeling session, was first published after World War II had started. It was Brown & Bigelow's best selling calendar for 1942 at a time when the company sold millions of calendars in America, and it became one of Armstrong's most reproduced pictures. Flowers was popular with American servicemen during World War II, some of whom sent her letters proposing marriage. Armstrong's calendars and silhouettes of Flowers were copied onto bombers and other planes as nose art and painted on tank turrets. She became so well known during the war, although more as a famous face than by name, that a serviceman's letter addressed simply as "Jewel Flowers, New York City" was delivered correctly. For many American servicemen abroad, she represented the "Why We Fight" spirit. U.S. President Franklin D. Roosevelt's government enlisted her to help promote war bonds. The January 1, 1945 edition of TIME magazine included Armstrong's "Toast of the Town" painting of Flowers in an article about Calendar Art. The article noted that calendars with "girl paintings" were "bought heavily by foundries, machine shops, auto-supply dealers."

Flowers married in 1946. She and her husband lived in several places while he tried a number of business ventures, including Laguna Beach, California, Greenville, South Carolina, Reno, Nevada, where she reportedly worked in as a card dealer for a time, and New York City. According to Michael Wooldridge, coauthor of Pin up Dreams: The Glamour Art of Rolf Armstrong, Armstrong called her a number of times during the period she was following her husband from place to place, to try to persuade her to return to New York and model for him.

Her modeling career ended with Armstrong's death in 1960. He left a large proportion of his personal wealth to Flowers. In total, Armstrong created around fifty to sixty works using Flowers as the model.

In the January 1930 issue of Screenland, Rolf Armstrong chose sixteen actresses to symbolize different colors. Here are the original captions and portraits in the order which they appeared in the magazine.[5]

White - Light could not be painted without it. No other color can take its place. - Mary Pickford